


One of Those Nights

by DRHPaints



Category: American (US) Actor RPF, Bill Hader - Fandom, Bill Hader RPF, Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF, US Comedians RPF
Genre: Anal Sex, Blow Jobs, Cunnilingus, Explicit Language, Explicit Sexual Content, Multi, One Shot, Oral Sex, Smut, Threesome, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex, threeway
Language: English
Status: Completed
Published: 2020-09-01
Updated: 2020-09-01
Packaged: 2021-03-06 15:07:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,961
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26240875
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Bill Hader and Gwendolyn Greene are guests on Conan’s talk show. After, the three of them go out for drinks and Gwendolyn invites them back to her place.
Relationships: Conan O’Brien/Bill Hader/Original Female Character
Comments: 9
Kudos: 9





	One of Those Nights

**Author's Note:**

> For those who are curious, the title comes from the song ‘One of Those Nights’ by Juicy J ft. The Weeknd. I just think it’s a sexy song.

Music dying down, Conan clapped his hands as they came back from commercial. “Alright everyone, we’re here with Bill Hader. Bill, now _Barry_ quickly became one of my favorite shows. It’s funny, smart, poignant…”

“Aw, thanks, buddy.” Bill smiled.

Conan brought an index finger to his lip. “So I’m wondering what it’s been like for you when you walk around now? I know it used to be everywhere you went, you’d get ‘Stefon! Stefon!,’ right? Are people calling you ‘Barry’ now?”

Closing his eyes and giggling, Bill nodded. “Yes. All the time. Airports, everywhere. Though I still get plenty of people approaching me about Stefon, too. But sometimes you get people who mix things up a little…” Smirking, Bill scratched his face. “For instance, I was in Louisiana and this guy came lumbering up to me in the airport, and in front of a huge group of people, he bellows,” Bill affected a heavy New Orlean accent. “Hey, aren’t you that queer fella who murders people?” 

Conan and the audience laughed. “And I just looked around like, um…” Bill plastered a terrified expression on his face, turning this way and that as if he were appealing to a crowd of strangers. “So yeah, sometimes causes problems.” 

Breaking out in giggles again, Conan threw to commercial and Bill switched over to the other chair so he could welcome the next guest. “Okay, next up, you’ve seen her in _Inpatient, Eye of Mortimer,_ and _The Tea-Stained Canvas._ She’s going to be starring in the new series _Analysis_ , please welcome, Gwendolyn Greene!”

A crimson-haired woman in a short black dress emerged from behind the curtain, waving to the audience before hugging Andy and Conan, who kissed her cheek before she sat down. Gwendolyn also turned and squeezed Bill’s forearm, smiling, before crossing her legs and facing Conan.

“Hey Gwendolyn, thanks for coming on the show. Or is it Gwen?”

Gwendolyn smirked. “You can call me whatever you want, Conan.”

“Oh, well…” Conan made his eyebrows dance, adjusted his tie, then growled at her. 

Audience laughing, Gwendolyn smiled. “Gwen is fine, thank you.”

“Great, so Gwen, you’ve got this new show coming out next month. Tell us what it’s about.” Conan ran a hand over his buoyant orange hair and sat back in his chair.

Tossing her hair over her shoulder, Gwendolyn lifted a strap of her dress that was slipping a little before responding. “Well, it’s about a therapist who gets involved with the world of BDSM and starts incorporating elements of that world into the treatment of her patients.”

“Wow.” Corners of his lips turned down appraisingly, Conan nodded. “Now…” He held up a hand. “This show is on HBO, correct?” 

“Yes.” Gwendolyn nodded.

“Okay, so…” Conan gestured to himself. “I am very…what’s the term for it?” Feigning deep thought for a moment, Conan popped his head up as if the answer suddenly came to him. “Catholic and repressed.” Gwendolyn laughed along with the audience. “Am I going to be able to enjoy this show?”

Putting her tongue to her teeth, Gwendolyn eyed Conan’s lanky form. “If anything, that’ll make you enjoy it _more._ ” Chuckling, Conan covered his reddening face. 

“Alright then, now I understand you’ve gathered some pretty interesting people together for this project.”

“Oh yeah.” Gwendolyn counted off on her fingers. “I mean, in addition to myself the cast has folks like Indya Moore, Patrick Fischler, J.K. Simmons...and the first three episodes were directed by Hiro Murai, who’s just—“

Bill grabbed her arm from the next chair. “Hiro Murai!” With a look of excitement on his face, Bill let go and sat back. “Oh sorry, it’s just...he directed four episodes of _Barry_ for us. The man is a genius.”

Emerald eyes looking over at him, Gwendolyn nodded. “I know, that’s why I suggested him to the producers. _Barry_ is brilliant.” She smiled.

Tipping his head from side to side, Bill grinned. “Thank you.”

They discussed her show a bit more before the interview came to a close, and afterward the three of them hung out chatting backstage. 

“Did you fellas want to go out and get a drink or something?” Gwendolyn looked between them.

“Oh.” Bill placed his hands on his thighs. “Sure.” He shrugged.

Conan nodded. “Yeah, just let me go scrub this makeup off my face. Be right back.” 

Once Conan disappeared, Bill leaned in a little. “So...Hiro Murai? His cinematography work is pretty amazing, right?”

Gwendolyn nodded. “Very impressive. I was blown away. I also particularly love what you did in the episodes you directed. I don’t know if anyone’s mentioned it to you, but, from my perspective at least, it was reminiscent of Andrzej Wajda’s work.”

Mouth dropping open, Bill touched her shoulder. “Oh my goodness, that’s _exactly_ what I was going for!”

“Ashes and Diamonds, right?” Gwendolyn smiled, pointing at him.

Closing his eyes, Bill nodded. “That’s rad, yes. Thank god someone got it.” Giggling, he shook his head. “Everybody keeps saying ‘Oh, that looks just like the Cohen brothers’.” Bill threw up his hands in exasperation. “Which, don’t get me wrong, I love them and that’s a tremendous compliment, but it wasn’t my intention.”

Chuckling, Gwendolyn patted his shoulder. “Well, regardless. It was beautiful.” Holding his cobalt gaze for a moment, Gwendolyn turned away when she noticed Conan’s tall figure coming down the hallway, tie discarded and top two buttons of his blue shirt undone.

“Alright, ready?” He clapped his freckled hands together. Gwendolyn nodded and the three of them left, heading to a bar nearby Conan recommended. Sliding into a booth, they ordered their drinks.

“Thanks again so much for having me on the show.” Gwendolyn smiled at Conan, touching his shoulder. “I’ve wanted to come on for such a long time.”

Conan nodded. “Of course, happy to have you.” He found his eyes trailing down to her cleavage, and had to remind himself to focus on her face. “Feel free to come back anytime you have a new project. God knows I’ve had Bill on more than enough times already.”

Giggling, Bill nodded. “Yeah, pretty sure I should be getting a writer’s credit at some point.”

“So Bill," Gwendolyn leaned over and Bill was suddenly extremely aware of the fact that her thigh was pressing up against his underneath the table. “Are you going to be doing another movie anytime soon, or are you focusing on _Barry_ for the time being?”

Taking a sip of his drink to calm himself, Bill tilted his head. “Well, I signed on for this _Empress of Serenity_ project a couple of years ago, a dramedy with Issa Rae, but we’ve had a bit of trouble getting it off the ground, so I’m not exactly sure when it will see the light of day.” He shrugged.

“Oh, well, I look forward to seeing it whenever it does.” Gwendolyn pulled her hair over her shoulder, and Bill caught himself examining the long line of her neck. “I love your dramatic work. _The Skeleton Twins_ in particular is one of my favorite films.”

Smiling humbly, Bill nodded. “Thank you, yeah. That was fun to make.”

Turning her attention to Conan, Gwendolyn’s viridescent eyes pierced his as she delicately placed her ivory fingers atop his large hand. “You know I am _loving_ the _Conan Without Borders_ shows.” Her eyebrow ticked up for half a second and Conan swallowed hard. “Pretty...amusing seeing you with that dominatrix in Germany.” Biting her lip just a little, Conan felt a shiver run through him.

“Yeah, um…” He gripped his glass. Gwendolyn’s hand still rested atop his own and he wasn’t sure what to do about it. “We had a great time over there. The people were amazing.”

Nodding, Gwendolyn sat back and sighed, finishing her drink and setting down her glass. “So…” She looked down at the table, a smirk growing on her face. “Do you want to come back to my place?”

Blinking rapidly, Bill turned to Conan, a similar expression of shock etched in his features. Opening his mouth hesitantly, Bill glanced over at her. “Um...Gwen? Which, uh...which one of us are you...are you asking, exactly?”

Tracing a finger around the rim of her glass, Gwendolyn peeked back and forth at them out of the corners of her eyes. “Is it a problem if I’m asking...both of you?”

Alarmed, Conan splayed his hands out on the table, looking to Gwendolyn, then meeting Bill’s dark blue eyes. They searched one another for a moment, before Bill’s gaze dropped to the table and his thumb wove through the condensation on his glass. Bill cleared his throat. “No, um...that’s...that’s not a problem for me…” Lifting the drink to his lips, he willed his hand not to shake as he awaited Conan’s response, hoping he hadn’t just made a years-long friendship painfully awkward for the foreseeable future.

Tapping the table with a finger, Conan blinked, picked up his drink, tossed it back, and shifted his eyes away. “Yeah...yeah, alright.”

“Great.” Gwendolyn beamed, sliding her hands under the table to pat both of their knees, which made Conan and Bill adorably squirmy. “Wanna get out of here?” Agreeing, they paid the check and she gave them directions to her house. 

Following Gwendolyn inside, Bill found he didn’t know what to do with his hands, and kept putting them in his pockets, only to take them out again, fidget, and try inserting them once more. Conan wasn’t faring much better. Nervously running his hand through his hair, his tongue darted over his lips as Gwendolyn led them to the kitchen.

“Do you guys want anything to drink? Beer? Wine?”

Bill shook his head. “No thanks, I’m alright.”

“I’m good.” Conan bobbed his head awkwardly, patting his thighs.

“Okay.” Gwendolyn smiled. “Wanna go upstairs then?”

Taking a deep breath and holding it, Bill slid his eyes over to Conan briefly before nodding. “Sure.” Conan replied, folding his lips under. Grinning, Gwendolyn directed them up the stairs and they watched her round hips switch with each step, hearts hammering forcefully in the ascent. 

Gwendolyn’s room was light and airy, tastefully appointed with a large bed decked out in a lavender duvet. Wasting no time, Gwendolyn turned around and grabbed the hemline of her dress, lifting it effortlessly overhead in one fluid motion, allowing the fabric to flutter to the floor.

Standing before them in a black lace bra and panties, Gwendolyn combed her fingers through her hair before sauntering up to Conan. Placing her hands on his chest, Conan didn’t know where to look until her hand tenderly cupped his sculpted jawline, drawing in his crystalline blue eyes and bringing her face close. Capturing his thin lips, Gwendolyn’s tongue snuck past Conan’s teeth as she pushed the jacket from his shoulders and it tumbled to the floor. Tilting her head, she wound her fingers into his fluffy orange hair, humming slightly as Conan’s hands found her waist and she began unbuttoning his shirt. Once she pulled it free of his slacks, Gwendolyn broke away, caressing Conan’s prominent cheekbone before stepping over to Bill.

Shifting his eyes back and forth, Bill willed his hands to stay still as Gwendolyn’s fingers crept into his chestnut waves. Noticing his substantial nerves, she brought her lips to the ear opposite Conan. “ _You okay, Bill?_ ” Whispering softly, her fingers played with the tendrils of hair at the back of his neck. Nodding, Bill’s sizable hands caressed her waist and she pulled back, joining to his light pink lips. 

In spite of his nerves, Gwendolyn was surprised at Bill’s voracity, fingers bunching in her mass of scarlet hair and tangling their tongues together passionately, other hand kneading her hip as she helped him out of his jacket and encouraged him to pull his t-shirt overhead, trailing her fingers over Bill’s firm chest. 

Parting from him, Gwendolyn took half a step back and held her hand out to Conan, lassoing him in. Stepping over, Conan looked to Bill for a moment before his freckled hands found Gwendolyn’s shoulders and he dipped down to brush his lips over her neck while her mouth connected to Bill’s. 

Hands behind her back, Gwendolyn unhooked her bra and tossed it aside. Both Conan and Bill reached for the same breast and their hands touched. Eyes meeting, they hastily looked away, choosing a side and beginning to caress her. 

Craning her neck back to Conan, Gwendolyn kissed him, rejoicing in the way he would start tender and tentative, growing insistent and demanding, holding her face and licking into her mouth greedily. Bill’s lips dragged over her collarbone as Gwendolyn reached back and pulled Conan’s hips against her ass, sliding herself up and down the outline of his stiff erection, provoking a soft moan against her lips. When Conan tilted his hips forward, rubbing against her, Gwendolyn nodded and rolled her ass back into him again.

Hand flowing over Bill’s smattering of dark chest hair, she continued down and palmed his cock over his slacks. Dark blue eyes studying her, Bill’s strong fingers stuttered down her abdomen before landing between her thighs, petting over her panties. Gwendolyn undid Bill’s fly and snaked her hand inside, encircling his thick cock and pumping lightly. Breath hitching, Bill’s fingers dipped inside and began working through the slickness surrounding her clit, Conan’s thrusts rocking her into his hand. 

Stopping to take off his undershirt, Conan crouched down and peeled Gwendolyn’s panties to the floor. Stepping out of them, she flipped around to face him, unzipping Conan’s slacks and working them off his narrow hips as Bill glided his cock into the crack of her ass through his boxers, large hands kneading her cheeks as he peppered kisses over her shoulders.

Grasping Conan’s long cock, Gwendolyn jerked him, thumb rubbing over the head as their tongued danced. Conan’s lengthy fingers fiddled with her clit until she was wet and needy. Gwendolyn dropped Conan’s boxers to the floor, looking back to fuse mouths with Bill as her wrist flew over Conan’s cock and he bent down to suck one of her nipples between his thin lips.

Mouths panting as Bill ground against her ass and Conan worked into the warm circle of her palm, Gwendolyn was moaning a little when she took half a step back, placed her hands on their shoulders, passing her eyes between them.

Blue eyes meeting, Bill swallowed and Conan looked at him with trepidation. Conan always assumed Bill wasn’t straight, he just gave off that energy. But Conan didn’t have much experience with men. Aside from that time in college, it wasn’t something he considered often. 

But he couldn’t deny Bill was handsome, so when Bill took half a step toward him, Conan lifted his hand, resting it gingerly on one of Bill’s expansive shoulders. Head tipped down, Bill’s eyes darted as he approached the taller man until Conan could feel his exhaling breath. Looking up, Bill’s oceanic eyes held an unexpected craving as he brought his face near. Lips meeting, at first the sensations were disorienting for Conan. Stubble under his fingertips as strong hands played with his orange hair and massaged his back, it took him a moment to accept. But as Bill’s tongue twirled into his mouth, fingers dancing over his freckled skin, Conan caught himself sinking into him, hand cupping the small of Bill’s back and shuffling forward. 

When their cocks accidentally brushed together, Conan jerked his hips backward and Bill broke away from their kiss. Glancing down between them, his thumb polished Conan’s cheek. “You okay, buddy?”

Nodding, Conan took a breath. “Yeah, sorry. Just...caught me off guard, I guess.” He chuckled.

Scrunching his fingers in Conan’s iconic hair, Bill smiled. “No problem.” Grinning, Conan felt Gwendolyn rub his shoulder and turned to her.

“Come on.” She took them both by the hand and crawled into the bed. Following, Conan laid along one side, meeting her lips, fingers dipping between her thighs while Bill settled on the other, kissing her neck and massaging her breasts. Gwendolyn took hold of both of their cocks, stroking, before Conan pulled away and began kissing his way down her body, pausing to draw a nipple between his thin lips, flicking his tongue over it, and lowering himself between her thighs.

Bill joined his mouth to Gwendolyn’s as Conan separated her legs and parted her lips, the tip of his tongue circling her clit. Digging his sculpted jaw forward, Conan began lapping her, and Gwendolyn rocked her pelvis against his eager face, moaning into Bill’s mouth. 

“Wait…” Gwendolyn gasped, pulling away.

Conan emerged. “What? Everything okay?”

“Yeah.” Gwendolyn nodded. “Let’s just switch positions. Get in a...a triangle, if that works for you guys.”

Bill and Conan looked at each other. Bill shrugged. “Sure, sounds good. Where should we…?” 

Gwendolyn caressed his stubbled jaw, nudging her nose against his cheek. “I really want to suck you, Bill.”

A shiver ran through Bill and he swallowed, nodding. “Okay.” He glanced at Conan. “Is that okay with you?”

Realizing what Bill was asking as he eyed his cock, Conan’s hand clenched reflexively and he cleared his throat. “Um...yeah. Yeah, that works.”

Triangulating themselves, Conan repositioned his face between Gwendolyn’s legs as she wrapped her fingers around Bill’s thick cock, taking the head into her mouth and sucking lightly. Scooting forward, Bill studied Conan, chiseled features working lustfully between Gwendolyn’s thighs as he tentatively placed his hand on his cock. 

Conan’s eye opened, peeking at Bill from the corner as his tongue extended, painting a broad strip from base to tip along Conan’s erection before sinking down and taking the entirety of his length into his hot, wet throat.

“ _Oh holy fuck._ ” Conan couldn’t help but gasp, forehead resting on Gwendolyn’s hip for a second as his freckled hand claimed the top of Bill’s head. Taking a couple of shallow breaths, Conan returned to Gwendolyn, locking his lips around her swollen clit and starting to suck, whipping his tongue around in a frenzy.

Bobbing and stroking in unison, Gwendolyn was moaning loudly around Bill’s cock as she rutted against Conan’s face, smearing the evidence of her desire across his cheeks. Mewling whines rose in Bill’s chest and one of his large hands guided Gwendolyn’s head, rolling his hips into her mouth.

Awash in the sensation of Bill’s throat, Conan shamelessly humped his face, fingers tearing at his dark hair and whimpering around Gwendolyn’s clit as Bill eagerly consumed his long cock. 

Letting Bill’s cock fall from her mouth, Gwendolyn continued to jerk wildly as her thighs clamped shut around Conan. “ _Oh fuck! I’m cumming! I’m cumming!_ ” Body quaking and free hand bunching in the sheets, Gwendolyn laid her head on Bill and took a moment to catch her breath. 

Turning from her, Conan took Bill’s head in both hands and began slamming into his throat, Bill moaning around his sensitive cock and caressing Conan’s chest while Conan writhed on the mattress. “ _Fuck yeah, suck me! Don’t stop! Yes! Fuck!_ ” Conan cried, then he felt Gwendolyn’s hand on his shoulder and her lips at his ear. 

“Do you want to fuck me, Conan? If not, no problem. You’re more than welcome to cum in Bill’s mouth. I’d love to watch.” Smiling mischieviously, Gwendolyn carded her fingers through Conan’s orange hair as his hips stilled. Lifting his hands, he looked down and Bill raised his head, wiping his eyes and mouth. 

Nodding, Bill ran a hand over his hair. “Yeah. Let’s fuck.”

Grinning, Gwendolyn bit her lip, rubbing Conan’s chest. “Do you want to fuck me in the ass?”

Eyes going wide, Conan nodded enthusiastically. “Yes. Definitely.”

“Okay.” Standing up, Gwendolyn motioned to Bill. “Lay down.” Rolling onto his back, Gwendolyn encouraged Bill to let the lower half of his legs hang over the edge of the bed. Rifling in her dresser, she unearthed two condoms and lube, passing the latter and one of the condoms to Conan, and rolling the other over Bill. Straddling him, Gwendolyn’s fingers ran over his face before she positioned herself and sank down on Bill’s turgid cock, throwing her head back at the delicious stretch.

“Ah _fuck_.” Gasping, she rotated her hips from side to side to better ensconce Bill before bending forward and tilting her head back to look expectantly at Conan.

Applying the condom, Conan smeared lube over himself and Gwendolyn before placing the head of his cock against her. “Ready?” Gwendolyn nodded and he tipped forward gradually, allowing her to acclimate to the sensation. Once fully sheathed, Conan placed a knee on the bed between Bill’s legs and began swiveling his hips.

It took them a couple of minutes, but soon they developed a robust rhythm, Gwendolyn bouncing between them as Bill’s thumb spun over her clit and Conan fondled her breasts from behind. Thighs pistoning, Gwendolyn’s speed increased as her fingertips dug into Bill’s chest. “ _Fuck! Yes! Yes! Just like that!_ ” Her moans rising to screams, Conan’s lip curled and he raised his free hand high to smack across her ass, pounding into her with abandon and forcing her down against Bill, increasing the friction between the three of them as the sound of clapping flesh and heavy breathing permeated the air.

Riding Bill’s cock boldly, Gwendolyn’s body fluttered around them. “ _Oh fuck! I’m cumming! Fuck! Yes!_ ” Eyes rolling, she ceased bouncing, hips dragging back and forth as her knees wove in and out, huffing moans tumbling from her lips.

After how close Bill brought him with his mouth, the increased pressure around Conan’s cock from Gwendolyn’s tight ass proved to be too much. With a guttural groan, he hooked an arm across her chest, body curving over her and panting into her back as his lanky body tensed. “ _Fuck, Gwen, fuck! You’re gonna make me cum...fuck!_ ” Strands of orange hair sticking to his pronounced forehead, Conan stayed inside her, still for a moment while he took a few deep breaths. Pulling out, Conan flopped back on the bed, limp and exhausted.

Pulsing inside of her gently, Bill lifted a hand to Gwendolyn’s face. “Is it okay if I still fuck you?”

Gwendolyn chuckled wearily. “Yeah, Bill. Of course.”

Bill rolled her onto her back, lifting a knee for leverage and drove deep inside, his dark eyes fiery. “Is it okay if I fuck you hard?”

“Oh _hell_ yes.” Lifting her eyebrows, Gwendolyn grinned and they kissed as Bill began rocketing into her, cramming his arm between them to finger her engorged clit. Limbs rattling on the mattress, Gwendolyn’s nails dug into Bill’s back. “ _Fuck! Yes! I’m gonna cum! Yes!_ ” Tightening around him, Bill let out a broken whimper and lay flat on top of her, face nestled in Gwendolyn’s neck, pelvis anxiously pumping as a high whine grew in his throat.

“ _Yeah! Fuck! Yeah! I’m cumming! Fuck! Fuck!_ ” Hips jittering erratically, Bill froze for a moment before collapsing above her, sweaty and sated. Eventually rolling off, Bill sought oxygen and Gwendolyn pushed her hair back from her face, coming up to her elbows. 

“Well fellas,” She swung her knees from side to side to nudge each of them. “That was great. Thanks.”

Conan’s hand flowed up her arm and he kissed Gwendolyn’s neck, resting his head on her shoulder. “Yeah, this was really fun.”

Laying on his side with his head propped up on his hand, Bill drew a circle around Gwendolyn’s navel before giggling a little. “I hope you don’t do this with all your guests…” Flicking his eyes up, Bill traced a finger across Conan’s forearm.

“No. Somehow I don’t think Martin Scorsese and Eartha Kitt would make for a very good time.” Conan smirked, and all three fell together laughing.

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also take requests!


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